A view over the Tuscan hills through umbrella pines and cypress trees

Tuscany

The part of Italy where doing less is the entire point, and the hardest thing to plan for.

Italy · 3–5 nights

Tuscany is the part of an Italy trip that people plan like a city and then wonder why it did not work. The whole value of the countryside is that nothing is scheduled, and an itinerary with three hill towns in a day removes exactly the thing you came for.

The good version looks almost empty on paper. One base, three to five nights, one thing a day at most, and long afternoons that belong to nobody. The days you remember here are the lunch that ran to four o'clock and the evening you did not drive anywhere.

Good for

Slow trips, and anyone who is tired
Food, wine, and cooking
Groups and multi-generational travel
Anniversaries and milestone birthdays

Suggested stay: 3–5 nights

Before you book

What people get wrong about Tuscany.

The practical things that change a trip, rather than a list of sights you can find anywhere.

Pick one base and stay in it

Val d'Orcia, Chianti, or just outside Siena. Moving every two nights is the most common Tuscany mistake and the easiest to avoid.

You need a car, or a driver

The countryside is not served by public transport in any useful way. If nobody wants to drive on unfamiliar roads after a long flight, a driver for the transfer days is money well spent.

A villa and an agriturismo are not the same thing

A villa is a house you have to yourself, usually with a pool and a kitchen. An agriturismo is a working farm with rooms and, often, the best dinner of your trip. Both are good; they suit different groups.

Book the long lunch

The meals that people describe for years afterwards are almost always arranged in advance, at a specific place, for a specific afternoon. They very rarely happen by accident.

From the road

Tuscany, as I found it.

Photographs from my own time in Tuscany. No stock, no borrowed shots.

A figure walking between vineyard rows at sunset in Tuscany

A stone Tuscan farmhouse with a terracotta roof and cypress trees beside it

Cafe tables and closed umbrellas on a stone street in a Tuscan hill village

A medieval stone arch opening onto a narrow street of shops

A bicycle leaning against a stone house with green shutters and a window box

A group of women on the steps of Siena cathedral beneath its striped marble facade

Kerry-Ann Stephens against a medieval stone wall in San Gimignano

A steep Siena street running down between brick buildings towards the rooftops

What it pairs with

Florence, which sits at the edge of it and makes the easiest arrival point, and Rome by train afterwards. Three nights in Florence and four in the countryside is a week that does not feel rushed.

The whole of Italy

Questions

Tuscany, answered.

How many days do you need in Tuscany?

Three nights is the minimum for it to feel like anything other than a drive. Four or five is where it starts doing what people hope it will do, which is slow the trip down.

Should you stay in Florence or in the countryside?

If you want museums and restaurants within walking distance, Florence, with day trips out. If you want the version with a pool, a view and no schedule, stay in the countryside and visit Florence for a day. Trying to do both properly in under a week is how trips get exhausting.

Do you need to speak Italian in rural Tuscany?

No, but it helps more here than in the cities. Enough to greet someone and order lunch goes a long way, and in the smaller places it changes how the afternoon goes.

Also worth your nights